Cobalt- versus ruthenium-catalyzed Alder-ene reaction for the synthesis of credneramide A and B

The Journal of Organic Chemistry
Florian Erver, Gerhard Hilt

Abstract

The first synthesis of the natural products credneramide A and B was accomplished by utilizing Alder-ene reactions between a terminal alkene and an internal alkyne to generate the rather uncommon 1,4-diene substructure of these compounds. Moreover, two different short linear sequences toward these targets are evaluated using either a cobalt-catalyzed Alder-ene reaction of 1-chloropent-1-yne or a ruthenium-catalyzed Alder-ene reaction of 1-trimethylsilyl-1-pentyne with 5-hexenoic acid derivatives in the key step transformation. In addition, saponification of the primary Alder-ene product derived from the cobalt-catalyzed Alder-ene reaction led to credneric acid, the biological precursor of both natural products.

References

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Sep 11, 2003·Chemical Reviews·Jesús A Varela, Carlos Saá
Oct 6, 2005·Angewandte Chemie·Barry M TrostMichael T Rudd
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Sep 28, 2007·Angewandte Chemie·Gerhard Hilt, Jonas Treutwein
Mar 5, 2009·Chemical Communications : Chem Comm·Gerhard Hilt, Jonas Treutwein
May 7, 2010·The Journal of Organic Chemistry·Anne-Laure AuvinetGerhard Hilt
Jun 17, 2011·Journal of Medicinal Chemistry·Lidia Martín-CouceSilvia Ortega-Gutiérrez

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